ES2628087T3 - Procedimiento para producir microcápsulas - Google Patents
Procedimiento para producir microcápsulas Download PDFInfo
- Publication number
- ES2628087T3 ES2628087T3 ES10167305.1T ES10167305T ES2628087T3 ES 2628087 T3 ES2628087 T3 ES 2628087T3 ES 10167305 T ES10167305 T ES 10167305T ES 2628087 T3 ES2628087 T3 ES 2628087T3
- Authority
- ES
- Spain
- Prior art keywords
- microcapsules
- isocyanate
- isocyanates
- emulsion
- premix
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
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- 239000003094 microcapsule Substances 0.000 title claims abstract description 75
- 238000000034 method Methods 0.000 title claims abstract description 44
- 239000012948 isocyanate Substances 0.000 claims abstract description 75
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 74
- 239000000203 mixture Substances 0.000 claims abstract description 52
- 239000000243 solution Substances 0.000 claims abstract description 31
- 239000000839 emulsion Substances 0.000 claims abstract description 28
- 239000007788 liquid Substances 0.000 claims abstract description 22
- 150000001412 amines Chemical class 0.000 claims abstract description 21
- 239000000084 colloidal system Substances 0.000 claims abstract description 21
- 230000008569 process Effects 0.000 claims abstract description 21
- 230000001681 protective effect Effects 0.000 claims abstract description 21
- 239000007864 aqueous solution Substances 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 8
- 239000011344 liquid material Substances 0.000 claims abstract description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 239000000463 material Substances 0.000 claims description 22
- 239000006185 dispersion Substances 0.000 claims description 19
- 229920002873 Polyethylenimine Polymers 0.000 claims description 14
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 14
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 14
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
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- 239000000123 paper Substances 0.000 claims description 5
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- 238000004140 cleaning Methods 0.000 claims description 2
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- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical group NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000542 sulfonic acid group Chemical group 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- 235000014113 dietary fatty acids Nutrition 0.000 description 25
- 239000000194 fatty acid Substances 0.000 description 25
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- 125000004432 carbon atom Chemical group C* 0.000 description 18
- SVYBEBLNQGDRHF-UHFFFAOYSA-N 4-amino-N-(5-ethyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide Chemical compound S1C(CC)=NN=C1NS(=O)(=O)C1=CC=C(N)C=C1 SVYBEBLNQGDRHF-UHFFFAOYSA-N 0.000 description 17
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- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 16
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- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 11
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- 239000002775 capsule Substances 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 9
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- 239000003242 anti bacterial agent Substances 0.000 description 8
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- 150000002191 fatty alcohols Chemical class 0.000 description 8
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- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 8
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- 239000011647 vitamin D3 Substances 0.000 description 8
- 229940021056 vitamin d3 Drugs 0.000 description 8
- VXIXUWQIVKSKSA-UHFFFAOYSA-N 4-hydroxycoumarin Chemical class C1=CC=CC2=C1OC(=O)C=C2O VXIXUWQIVKSKSA-UHFFFAOYSA-N 0.000 description 7
- 230000000895 acaricidal effect Effects 0.000 description 7
- 239000000642 acaricide Substances 0.000 description 7
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- 125000000217 alkyl group Chemical group 0.000 description 7
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- 231100000614 poison Toxicity 0.000 description 7
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 6
- 125000000129 anionic group Chemical group 0.000 description 6
- 229940088710 antibiotic agent Drugs 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
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- 238000010438 heat treatment Methods 0.000 description 6
- 229960002523 mercuric chloride Drugs 0.000 description 6
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- NHZLNPMOSADWGC-UHFFFAOYSA-N 4-amino-N-(2-quinoxalinyl)benzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CN=C(C=CC=C2)C2=N1 NHZLNPMOSADWGC-UHFFFAOYSA-N 0.000 description 5
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- 241000233866 Fungi Species 0.000 description 5
- 208000032843 Hemorrhage Diseases 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
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- 239000006011 Zinc phosphide Substances 0.000 description 5
- HEAHZSUCFKFERC-IWGRKNQJSA-N [(2e)-2-[[4-[(e)-[7,7-dimethyl-3-oxo-4-(sulfomethyl)-2-bicyclo[2.2.1]heptanylidene]methyl]phenyl]methylidene]-7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl]methanesulfonic acid Chemical group CC1(C)C2CCC1(CS(O)(=O)=O)C(=O)\C2=C\C(C=C1)=CC=C1\C=C/1C(=O)C2(CS(O)(=O)=O)CCC\1C2(C)C HEAHZSUCFKFERC-IWGRKNQJSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 231100000636 lethal dose Toxicity 0.000 description 5
- BARWIPMJPCRCTP-CLFAGFIQSA-N oleyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC BARWIPMJPCRCTP-CLFAGFIQSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- HOKBIQDJCNTWST-UHFFFAOYSA-N phosphanylidenezinc;zinc Chemical compound [Zn].[Zn]=P.[Zn]=P HOKBIQDJCNTWST-UHFFFAOYSA-N 0.000 description 5
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 5
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- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 5
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- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
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- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
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- 239000004474 valine Substances 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/06—Making microcapsules or microballoons by phase separation
- B01J13/14—Polymerisation; cross-linking
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/06—Making microcapsules or microballoons by phase separation
- B01J13/14—Polymerisation; cross-linking
- B01J13/16—Interfacial polymerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/71—Monoisocyanates or monoisothiocyanates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Manufacturing & Machinery (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Polyurethanes Or Polyureas (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10167305.1A EP2399667B1 (en) | 2010-06-25 | 2010-06-25 | Process for producing microcapsules |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2628087T3 true ES2628087T3 (es) | 2017-08-01 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10167305.1T Active ES2628087T3 (es) | 2010-06-25 | 2010-06-25 | Procedimiento para producir microcápsulas |
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| Country | Link |
|---|---|
| US (1) | US20130095158A1 (enExample) |
| EP (1) | EP2399667B1 (enExample) |
| JP (1) | JP5934703B2 (enExample) |
| KR (1) | KR101925269B1 (enExample) |
| CN (1) | CN102958597B (enExample) |
| BR (1) | BR112012032634B1 (enExample) |
| CA (1) | CA2803420C (enExample) |
| ES (1) | ES2628087T3 (enExample) |
| MX (1) | MX341671B (enExample) |
| RU (1) | RU2572889C2 (enExample) |
| WO (1) | WO2011160733A1 (enExample) |
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| WO2013006661A2 (en) | 2011-07-06 | 2013-01-10 | President And Fellows Of Harvard College | Multiple emulsions and techniques for the formation of multiple emulsions |
| CA2882427A1 (en) * | 2012-08-28 | 2014-03-06 | Basf Se | Carrier system for fragrances |
| JP6143078B2 (ja) * | 2013-05-13 | 2017-06-07 | 清水建設株式会社 | 模擬粉体の製造方法、及び粉体飛散状態評価方法 |
| JP2014221012A (ja) * | 2013-05-13 | 2014-11-27 | 清水建設株式会社 | 模擬粉体、粉体飛散状態評価方法、及び粉体取扱い施設 |
| CN103933014B (zh) * | 2013-12-31 | 2016-03-09 | 杭州师范大学 | 一种肿瘤细胞靶向载药微胶囊 |
| GB2509431B (en) * | 2014-03-26 | 2016-09-14 | Rotam Agrochem Int Co Ltd | Herbicidal composition, a method for its preparation and the use thereof |
| EP3137207B1 (en) * | 2014-04-29 | 2019-02-06 | Basf Se | Anionic polyvinyl alcohol copolymer as protective colloid for pesticidal polyurea microcapsules |
| RU2619331C2 (ru) * | 2014-10-10 | 2017-05-15 | Александр Александрович Кролевец | Способ получения нанокапсул умифеновира (Арбидола) в альгинате натрия |
| WO2016061095A1 (en) * | 2014-10-14 | 2016-04-21 | President And Fellows Of Harvard College | Microcapsules and uses thereof |
| RU2599885C2 (ru) * | 2014-11-05 | 2016-10-20 | Александр Александрович Кролевец | Способ получения нанокапсул умифеновира (арбидола) в каррагинане |
| EP3215265B1 (en) | 2014-11-07 | 2019-06-19 | Basf Se | Process for preparing microcapsules having a polyurea shell and a lipophilic core material |
| KR102547707B1 (ko) | 2014-11-07 | 2023-06-23 | 지보당 에스아 | 캡슐 조성물 |
| CN107106469B (zh) | 2014-11-07 | 2021-03-12 | 奇华顿股份有限公司 | 有机化合物中或与之相关的改进 |
| KR20170078805A (ko) | 2014-11-07 | 2017-07-07 | 바스프 에스이 | 히드록시알킬 셀룰로오스를 포함하는 마이크로캡슐 |
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| US20230247986A1 (en) | 2020-06-26 | 2023-08-10 | Bayer Aktiengesellschaft | Aqueous capsule suspension concentrates comprising biodegradable ester groups |
| EP4190439A4 (en) * | 2020-07-31 | 2024-08-14 | Morishita Jintan Co., Ltd. | METHOD FOR PRODUCING MICROCAPSULES |
| WO2022028706A1 (de) | 2020-08-06 | 2022-02-10 | Symrise Ag | Bioabbaubare polyharnstoff/polyurethan-mikrokapseln |
| KR20230045063A (ko) | 2020-08-06 | 2023-04-04 | 시므라이즈 아게 | 폴리우레아/폴리우레탄 마이크로캡슐 |
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| WO2023147855A2 (de) | 2022-02-02 | 2023-08-10 | Symrise Ag | Verfahren zur herstellung von mikrokapseln |
| US20250144589A1 (en) | 2022-02-02 | 2025-05-08 | Symrise Ag | Method for Producing Microcapsules |
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| CN117296839B (zh) * | 2023-11-27 | 2024-02-23 | 山东华实药业有限公司 | 免活化稳定性二氧化氯消毒剂及其生产工艺 |
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| ATE65159T1 (de) * | 1986-10-23 | 1991-08-15 | Ciba Geigy Ag | Bekaempfung von ektoparasiten. |
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2010
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2011
- 2011-03-05 US US13/805,549 patent/US20130095158A1/en not_active Abandoned
- 2011-03-05 CN CN201180031169.8A patent/CN102958597B/zh not_active Expired - Fee Related
- 2011-03-05 JP JP2013515739A patent/JP5934703B2/ja not_active Expired - Fee Related
- 2011-03-05 KR KR1020127033516A patent/KR101925269B1/ko not_active Expired - Fee Related
- 2011-03-05 BR BR112012032634-1A patent/BR112012032634B1/pt not_active IP Right Cessation
- 2011-03-05 RU RU2013101538/05A patent/RU2572889C2/ru active
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- 2011-03-05 WO PCT/EP2011/001098 patent/WO2011160733A1/en not_active Ceased
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| BR112012032634A2 (pt) | 2018-01-23 |
| CA2803420C (en) | 2018-05-01 |
| CN102958597B (zh) | 2015-05-13 |
| WO2011160733A1 (en) | 2011-12-29 |
| RU2013101538A (ru) | 2014-07-27 |
| MX2012015042A (es) | 2013-06-28 |
| EP2399667A1 (en) | 2011-12-28 |
| MX341671B (es) | 2016-08-30 |
| JP5934703B2 (ja) | 2016-06-15 |
| KR101925269B1 (ko) | 2018-12-05 |
| CN102958597A (zh) | 2013-03-06 |
| RU2572889C2 (ru) | 2016-01-20 |
| BR112012032634B1 (pt) | 2018-12-26 |
| EP2399667B1 (en) | 2017-03-08 |
| KR20130121697A (ko) | 2013-11-06 |
| JP2013537472A (ja) | 2013-10-03 |
| CA2803420A1 (en) | 2011-12-29 |
| US20130095158A1 (en) | 2013-04-18 |
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